Menu

Javascript is not activated in your browser. This website needs javascript activated to work properly.
You are here

Enantioselective formal synthesis of tridemethylisovelleral

Author:
  • Daniel Röme
  • Martin H Johansson
  • Olov Sterner
Publishing year: 2007
Language: English
Pages: 635-638
Publication/Series: Tetrahedron Letters
Volume: 48
Issue: 4
Document type: Journal article
Publisher: Elsevier

Abstract english

A simple and efficient synthetic route to the bicyclic alpha,beta-unsaturated beta-keto ester methyl (3aS,7aS)-6-oxo-2,3,3a,6,7,7ahexahydro-1H-indene-5-carboxylate, a versatile intermediate in the synthesis of biologically active unsaturated 1,4-dialdehydes, is described. The synthesis includes a chirality introducing nonenzymatic asymmetric desymmetrization (ADS) reaction of a cyclic nieso-anhydride 4 and a modified Hofmann method for preparing exocyclic dienes. The ester was synthesized in a moderate overall yield (19%) from 6 and with an excellent enantioselectivity (> 90%).

Keywords

  • Organic Chemistry

Other

Published
  • ISSN: 0040-4039
Olov Sterner
E-mail: olov.sterner [at] science.lu.se

Dean

Faculty of Science

+46 46 222 82 13

+46 70 530 66 49

B127

Sölvegatan 27, Lund

39

Professor

Centre for Analysis and Synthesis

+46 46 222 82 13

1